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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:24:55 UTC

Update Date

2023-02-21 17:25:41 UTC

HMDB ID

HMDB0037174

Secondary Accession Numbers

HMDB37174

Metabolite Identification

Common Name

p-Mentha-2,4(8)-dien-9,3-olide

Description

p-Mentha-2,4(8)-dien-9,3-olide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. p-Mentha-2,4(8)-dien-9,3-olide is a coconut, coumarin, and hay tasting compound. Based on a literature review very few articles have been published on p-Mentha-2,4(8)-dien-9,3-olide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    4    6                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    1    3    5                                                  
CONECT    7    2    8   10                                                  
CONECT    8    4    7    9                                                  
CONECT    9    5    8   12                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-dihydro-3,6-Dimethyl-2(4H)-benzofuranone, 9ci	HMDB
Dehydromenthofurolactone	HMDB
FEMA 3755	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

3,6-dimethyl-2,4,5,6-tetrahydro-1-benzofuran-2-one

Traditional Name

3,6-dimethyl-5,6-dihydro-4H-1-benzofuran-2-one

CAS Registry Number

80417-97-6

SMILES

CC1CCC2=C(C)C(=O)OC2=C1

InChI Identifier

InChI=1S/C10H12O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5-6H,3-4H2,1-2H3

InChI Key

ZRTWVYJNKXXDDT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037174)
Cytoplasm (HMDB: HMDB0037174)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037174)

Source

Exogenous

Exogenous (HMDB: HMDB0037174)

Food

Food (HMDB: HMDB0037174)

Endogenous

Plant

Plant (HMDB: HMDB0037174)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037174)

Biological role

Nutrient (HMDB: HMDB0037174)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.05	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.67 m³·mol⁻¹	ChemAxon
Polarizability	18.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.775	31661259
DarkChem	[M-H]-	133.369	31661259
DeepCCS	[M+H]+	138.217	30932474
DeepCCS	[M-H]-	134.39	30932474
DeepCCS	[M-2H]-	171.871	30932474
DeepCCS	[M+Na]+	147.41	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.81 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9632 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2120.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	412.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	265.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	542.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	535.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1080.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1199.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	531.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	116.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Mentha-2,4(8)-dien-9,3-olide	CC1CCC2=C(C)C(=O)OC2=C1	2397.9	Standard polar	33892256
p-Mentha-2,4(8)-dien-9,3-olide	CC1CCC2=C(C)C(=O)OC2=C1	1434.9	Standard non polar	33892256
p-Mentha-2,4(8)-dien-9,3-olide	CC1CCC2=C(C)C(=O)OC2=C1	1462.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-06di-4900000000-7a1b2cd8f1798aafb7b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 10V, Positive-QTOF	splash10-014i-1900000000-8742610260dd2bb76938	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 20V, Positive-QTOF	splash10-00kb-9300000000-5088d6447bf54ae1d183	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 40V, Positive-QTOF	splash10-0uxu-9100000000-159bfbab6756951a7ff7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 10V, Negative-QTOF	splash10-03di-0900000000-567d1c93bef6783c061f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 20V, Negative-QTOF	splash10-03xr-0900000000-135536de361a78dac028	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 40V, Negative-QTOF	splash10-014i-5900000000-48125e1ed11c8be723bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 10V, Negative-QTOF	splash10-03di-0900000000-8db47caa9667c101bd0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 20V, Negative-QTOF	splash10-03di-0900000000-8fb7db590472594ec710	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 40V, Negative-QTOF	splash10-03xu-4900000000-b3aa822c1a008eb10b0c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 10V, Positive-QTOF	splash10-014i-0900000000-6635bd52a0126eebc59c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 20V, Positive-QTOF	splash10-014i-0900000000-c735e61e85a1c8a72aac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Mentha-2,4(8)-dien-9,3-olide 40V, Positive-QTOF	splash10-00mo-9300000000-a7988f65822c44b5a10c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016170

KNApSAcK ID

Not Available

Chemspider ID

2286344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3018936

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for p-Mentha-2,4(8)-dien-9,3-olide (HMDB0037174)

MOL for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

3D MOL for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

3D SDF for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

3D-SDF for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

PDB for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

3D PDB for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

SMILES for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

INCHI for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

Structure for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

3D Structure for HMDB0037174 (p-Mentha-2,4(8)-dien-9,3-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra